I have met lots of people who have regretted they retired from the workforce.  I met one former co-worker who squandered his 401k and now is trying to live off Social Security benefits that he took at age 62.  You get reduced benefits at that age in comparison to age 65 (at least for baby boomers such as me).  So, this former co-worker is now selling boiled peanuts to try to make up for blowing all his hard-earned 401k just 3 years after retiring.  That's right, he's selling peanuts and making peanuts as a result.  He hit me up for a loan not long ago.  Of course, I turned him down because there is simply no way he could ever repay me.
 
As a result, he no longer has anything to do with me now.  It is not my fault he doesn't know how to manage money.  This is something he should have thought about long ago.  Anyway, back to the subject....as I have stated before there can be regrets about retiring for several reasons.  Some did not consider the money that will be needed for health issues as you grow older.  Medicare cannot and will not cover all medical expenses.  Thusly, I decided to keep my Blue Cross/Blue Shield plan after retirement.   People think I'm crazy for having two health care insurance plans with BC/BS and Medicare.  But, considering what Obamacare will do to insurance premiums in the future, I am looking like the wily old fox.  Less and less is being covered by Medicare.  BC/BS picks up the remainder of my bills when I go into the hospital like I did for Diverticulitis earlier this year.

There are retirement regrets about everything from loss of companionship of co-workers on a daily basis to boredom.   I've covered some of these regrets in other retirement posts.  But, it seems I hear more and more about regrets of retirement as the years roll by.  In November, I will be retired ten years.  That simply doesn't seem possible to me.  It's too late for me to be really regretful about retirement. You can easily overcome other retirement regrets mentioned such as boredom, lack of companionship and other non-monetary complaints.  The regret about lack of money is not so easily overcome.  Some people have to "un-retire" and get a job to help pay expenses.  That's easier said than done.  It's tough on Senior citizens to find a job in a good economy.  It is far tougher in a bad economy (despite what you may read or hear from the news media).  Do I have regrets? In some ways I can say,  yes, I do.  Financially, I'm doing ok.  But, ten years into my retirement, I admit to boredom.  I do find things to keep myself occupied.  I do and have considered volunteer work in my spare time. But, even that gets old after a period of time.  You start thinking about each big event in your life.  You graduate from high school, college, get a job, get married, and then you retire.  After that, there is only one big event left....and you really don't want to spend much time thinking about that.

There are a lot of people who have regrets about retirement.  I was one of them at one time.  I guess it takes a couple of years to get accustomed to not having a job to go to each day after working for 30-40 years.  If there is any advice I can impart to you about retirement, it is the following;  1.  Set a goal for how much you want to save for retirement.  That is probably the best sage advice I can offer.  There are so many people who regret they did not save enough or even save at all for retirement.  2.  Think about the one thing you have always enjoyed doing and DO IT!   With me, it was my writing.  I finally published that novel I always wanted to do after I retired.  Find something to do that you never get bored of doing.  This is really important.  3. Finally, make sure you are mentally ready for retirement.  Lots of people look forward to retirement.  It's all I ever talked about when I was working every day.  But, be prepared for a life changing event.  Because, essentially, that is what retirement is, a life changing event.  Your life is changed from the everyday grind to a grind of not having to grind it out each day.  Some say they can't wait for that day.  I hope you really mean that.  In fact, make sure you mean that before you retire.  Retirement can be years of enjoyment if you prepared properly.  But, it also can be a life of regrets, about retirement, if you are not prepared.